Portland, Maine — Katie Lee Jacobs

For my parents 35th Anniversary, we promised them our first family trip in quite some time — kid free! After debating on a few different locations, we landed on Portland, Maine. None of us had been before, and it was extremely easy to get to (especially from NYC - just a short 1 hour flight!) Portland recently landed at the top of our domestic travel destinations for it’s food, brewery, and shopping scene. It was even named Bon Appetit’s 2018 City of the Year. So, we thought what better way to see what the buzz is about?

After picking the destination, we spend the rest of our time planning our itinerary, meals, and activities, and narrowing down hotel or or airbnb options. In this case, there were so many great places to pick from, but we ended up picking the Press Hotel as it was downtown Portland, and within walking distance to a lot of the destinations we wanted to go to. We definitely want to go back someday, and when we do, we want to stay near Kennebunkport at Hidden Pond.

DAY ONE: Portland

On our first full day in Portland, we sat down for a quick (but delicious) brunch at Union, which was conveniently located in our hotel. To follow, we walked around Portland, specifically the shops on Commercial Street and Exchange Street. You could easily meander through these adorable shops for a few hours. We built up quite an appetit from all of our shopping, so we popped into High Roller for some lobster and fries - YUM! Super cute place, and my husband left with a hat from the merch shop to commemorate the trip.

After lunch, we drove 20 minutes north to go to the Flagship LL Bean store which is in Freeport. If you’re heading this way, I’ve heard Harraseeket Lunch and Lobster Company is a must-stop for Lobsters. We had just gotten our Lobster fix at High Roller, so we skipped this stop, but spent some time walking around the insane LL Bean Store, and I bought this cute tote and added my (somewhat new) monogram.

On our way back to Portland, we stopped at Allagash Brewery for a beer flight and games. They have a great outdoor space where we hung out for the afternoon. That night, we opted for a casual dinner at The Grill Room. Not a must-stop in my opinion (I’d check out Fore Street, Eventide, Central Provisions, or The Drifter’s Wife instead!)

DAY TWO: Ogunquit + Portland + Kennebunkport

We decided to make the most of this gorgeous day, so we left the hotel around 7:30AM and drove down to nearby Ogunquit. Here, we went for a leisurely walk along Marginal Way, one of New England’s only paved footpaths along the ocean. It was absolutely beautiful! If you’re looking for a beach day, I’d recommend you bring your swim suit and find a spot along your walk. We had afternoon plans back in Portland, so we grabbed a quick breakfast at the Wild Blueberry and headed back to town. If you’re looking for a healthier option, Love Shack Juicery is right across the street and has great smoothies and juices.

Back in Portland, we hoped on a boat for our afternoon with Lucky Catch, a 90 minute excursion on the waters of Casco Bay, where we learned about the daily routines of a Maine Lobsterman. Afterwards, the caught lobsters can be purchased for wholesale “boat price” and either taken to go or next door to the Portland Lobster Company restaurant. We opted to take it next door and had the restaurant cook up our lobster — they added corn, fries, and coleslaw for a well-rounded meal.

After a busy, busy morning and afternoon, we did a little relaxing before our evening plans. We went to the famed Colony Hotel, which looks out over the Atlantic Ocean, for sunset cocktails. They have live music on Thursdays, Fridays, and Saturdays. For dinner, we planned a very special evening at Earth at Hidden Pond. We were able to book our dinner reservation within the Potting Shed, which was the perfect location to celebrate my parents 35th wedding anniversary. They’ve taken a space essential to successful gardening, and transformed it into a charming, artfully decorated private dining space. The walls are filled with hanging hurricane lanterns, vintage gardening tools and the occasional birdhouse. Lush, green plants are sprinkled around the room, further immersing you in the natural environment. And the food was absolutely to die for. Everything was so fresh and delicious. Potting Shed or not — this is a must-stop in my opinion!

DAY THREE: Kennebunkport

We started our morning with a quick bike ride through town to Tandem Bakery, where we ordered (and quickly devoured) the most incredible biscuit filled with butter and jelly (see here for a visual!) I’m glad we didn’t try this until our last day or we would have totally eaten these each morning. Standard Baking Company also came highly recommended.

Mid-Morning, we drove to Kennebunkport to walk around Dock Square before our sailing cruise with Schooner Eleanor. Unfortunately, it started to downpour just as we arrived and our sailing cruise was cancelled (such a bummer!) So we spent our afternoon shopping in Dock Square, which is located along the ocean and Kennebunk River. It was settled in the 1600’s and was a long time ship building mecca. We grabbed lunch at The Clam Shack with Ice cream to follow at Rococo Artisan Ice Cream (they have fourteen delectable flavors in their rotation!)

Thankfully the weather turned around and we hopped on the Kennebunkport Trolly for a drive along Ocean Avenue, filled with picturesque pull off points filled with flowers, cliffs and ocean views. Here, you’ll also see the Bush Compound in the distance.

On our way back to Portland, we stopped at the Portland Head Lighthouse in Cape Elizabeth for a quick family portrait and history lesson. That evening, we went to Scales for a delicious seafood dinner (great spot!) and grabbed drinks at Portland Hunt & Alpine Club afterward.

While we certainly covered a lot, I’m looking forward to coming back someday!